Tagetnoic acid, a new lipoxygenase inhibitor peroxy fatty acid from Tagetes minuta growing in Saudi Arabia.

A new peroxy fatty acid, tagetnoic acid (5) [4-((3S,6S)-6-((3E,8E)- octadeca-3,8-dien-1-yl)-3,6-dihydro-1,2-dioxin-3-yl)butanoic acid] and four known metabolites: ecliptal (5-formyl-a-terthiophene) (1), 5-(4-hydroxybut-1-ynyl)-2,20-bithiophene (2), 22,23-dihydrospinasterone (3), and stigmasterol (4) were separated from the n-hexane fraction of the aerial parts of Tagetes minuta L. (Asteraceae). Their chemical structures were verified using IR, UV, 2D and 1D NMR, and HRMS. Compounds 3-5 displayed potent lipoxygenase inhibitory potential with IC₅₀s 2.26, 1.83, and 1.17 lM, respectively compared to indomethacin (IC₅₀ 0.89 lM). Moreover, molecular docking study revealed that the potent activity of 5 is due to H-bonding and hydrophobic interaction. The results of this study suggested that Tagetes minuta dietary consumption would be useful for the individuals at risk of acute and chronic inflammatory disorders. [ABSTRACT FROM AUTHOR]